Triethyl phosphite → Diethyl 3-aminobenzylphosphonate

HRID 964637Notes

Reaction equation

HRID 964637 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-])=O.[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>C1COCC1.O>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Product 1

HCID 19077611Diethyl 3-aminobenzylphosphonate

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Following the procedure described in part E of Example 1 (R), (S)-α-[[2-[((1,1-dimethylethyl)dimethylsilyl)oxy]-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl]amino]-4-methoxybenzeneacetic acid was condensed with diethyl 3-aminobenzylphosphonate to generate the title compound. The diethyl 3-aminobenzylphosphonate was prepared by sequential treatment of commercial 3-nitrobenzyl bromide with triethyl phosphite at 125° C. for 6 hours followed by reduction with Na2S2 O4 in THF/H2O at 100° C.

Sources & evidence

ORD record
ord-c8d5cda530b74976bb0aac68bb9f3538
Source dataset
uspto-grants-1998_06
Patent number
US05770615

Reaction notes

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